CA2763574C - Process for the synthesis of 3-methyl-pyridine - Google Patents
Process for the synthesis of 3-methyl-pyridine Download PDFInfo
- Publication number
- CA2763574C CA2763574C CA2763574A CA2763574A CA2763574C CA 2763574 C CA2763574 C CA 2763574C CA 2763574 A CA2763574 A CA 2763574A CA 2763574 A CA2763574 A CA 2763574A CA 2763574 C CA2763574 C CA 2763574C
- Authority
- CA
- Canada
- Prior art keywords
- process according
- paracetaldehyde
- reaction
- mol
- formaldehyde
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 26
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 8
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 27
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 23
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 12
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims abstract description 5
- 230000014759 maintenance of location Effects 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 3
- MFEIKQPHQINPRI-UHFFFAOYSA-N 3-Ethylpyridine Chemical compound CCC1=CC=CN=C1 MFEIKQPHQINPRI-UHFFFAOYSA-N 0.000 claims description 10
- 239000006227 byproduct Substances 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AURDEEIHMPRBLI-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1.CC1=CC=CN=C1 AURDEEIHMPRBLI-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- 240000003834 Triticum spelta Species 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- -1 ammonia compound Chemical class 0.000 description 1
- 239000012045 crude solution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000016507 interphase Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/08—Preparation by ring-closure
- C07D213/09—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles
- C07D213/10—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles from acetaldehyde or cyclic polymers thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09008251.2 | 2009-06-24 | ||
| EP09008251A EP2277864A1 (de) | 2009-06-24 | 2009-06-24 | Syntheseprozess für 3-Methylpyridin |
| PCT/EP2010/003773 WO2010149352A2 (de) | 2009-06-24 | 2010-06-23 | Syntheseprozess für 3-methylpyridin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2763574A1 CA2763574A1 (en) | 2010-12-29 |
| CA2763574C true CA2763574C (en) | 2014-04-29 |
Family
ID=41119468
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2763574A Expired - Fee Related CA2763574C (en) | 2009-06-24 | 2010-06-23 | Process for the synthesis of 3-methyl-pyridine |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US9701634B2 (de) |
| EP (2) | EP2277864A1 (de) |
| JP (1) | JP5642780B2 (de) |
| KR (1) | KR20120031222A (de) |
| CN (1) | CN102803215B (de) |
| AU (1) | AU2010265076A1 (de) |
| BR (1) | BRPI1016148A2 (de) |
| CA (1) | CA2763574C (de) |
| DK (1) | DK2445880T3 (de) |
| EA (1) | EA201200047A1 (de) |
| IN (1) | IN2012DN00475A (de) |
| MX (1) | MX2011013687A (de) |
| PL (1) | PL2445880T3 (de) |
| WO (1) | WO2010149352A2 (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112679417A (zh) * | 2020-12-31 | 2021-04-20 | 兄弟科技股份有限公司 | 一种3-甲基吡啶的合成方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2700042A (en) * | 1952-08-30 | 1955-01-18 | Robert S Aries | Production of pyridine and beta picoline |
| GB1005984A (en) * | 1963-05-16 | 1965-09-29 | Ici Ltd | Manufacture of pyridine and alkylpyridines |
| FR2161128A5 (en) * | 1971-11-15 | 1973-07-06 | Nippon Steel Chemical Co | Pyridines prepn using copper catalyst |
| ATE5719T1 (de) * | 1980-05-23 | 1984-01-15 | Lonza Ag | Verfahren zur herstellung von 3-picolin. |
| FI814007A7 (fi) * | 1981-01-09 | 1982-07-10 | Lonza Ag | Menetelmä 3-pikoliinin valmistamiseksi. |
| CH660733A5 (de) * | 1981-09-29 | 1987-06-15 | Lonza Ag | Verfahren zur herstellung von 3-picolin. |
| CN1903842A (zh) * | 2005-07-29 | 2007-01-31 | 浙江爱迪亚营养科技开发有限公司 | 3－甲基吡啶的制备方法 |
-
2009
- 2009-06-24 EP EP09008251A patent/EP2277864A1/de not_active Ceased
-
2010
- 2010-06-23 IN IN475DEN2012 patent/IN2012DN00475A/en unknown
- 2010-06-23 CN CN201080028406.0A patent/CN102803215B/zh not_active Expired - Fee Related
- 2010-06-23 AU AU2010265076A patent/AU2010265076A1/en not_active Abandoned
- 2010-06-23 EA EA201200047A patent/EA201200047A1/xx unknown
- 2010-06-23 BR BRPI1016148-1A patent/BRPI1016148A2/pt not_active IP Right Cessation
- 2010-06-23 CA CA2763574A patent/CA2763574C/en not_active Expired - Fee Related
- 2010-06-23 KR KR1020127000726A patent/KR20120031222A/ko not_active Withdrawn
- 2010-06-23 DK DK10747156.7T patent/DK2445880T3/da active
- 2010-06-23 EP EP10747156A patent/EP2445880B1/de not_active Not-in-force
- 2010-06-23 WO PCT/EP2010/003773 patent/WO2010149352A2/de not_active Ceased
- 2010-06-23 JP JP2012516569A patent/JP5642780B2/ja not_active Expired - Fee Related
- 2010-06-23 MX MX2011013687A patent/MX2011013687A/es not_active Application Discontinuation
- 2010-06-23 PL PL10747156T patent/PL2445880T3/pl unknown
- 2010-06-24 US US12/822,770 patent/US9701634B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI1016148A2 (pt) | 2015-09-01 |
| WO2010149352A3 (de) | 2011-06-23 |
| PL2445880T3 (pl) | 2013-07-31 |
| CA2763574A1 (en) | 2010-12-29 |
| CN102803215B (zh) | 2014-04-30 |
| DK2445880T3 (da) | 2013-04-22 |
| MX2011013687A (es) | 2012-04-19 |
| EP2277864A1 (de) | 2011-01-26 |
| EA201200047A1 (ru) | 2012-08-30 |
| US9701634B2 (en) | 2017-07-11 |
| IN2012DN00475A (de) | 2015-06-05 |
| EP2445880A2 (de) | 2012-05-02 |
| US20110003997A1 (en) | 2011-01-06 |
| WO2010149352A2 (de) | 2010-12-29 |
| AU2010265076A1 (en) | 2012-01-19 |
| KR20120031222A (ko) | 2012-03-30 |
| JP2012530738A (ja) | 2012-12-06 |
| CN102803215A (zh) | 2012-11-28 |
| EP2445880B1 (de) | 2013-01-23 |
| JP5642780B2 (ja) | 2014-12-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20200831 |